A Sissy's Place

Mistress Victoria's favorite strap-on.

Mistress Victoria's favorite strap-on.

I had a fun experience last night.  Jared contacted me wanting to be made into a sissy.  He didn't know how deep that rabbit hole went! When he showed up, I was dressed in a French maid outfit, the miniskirt not making it even halfway down my smooth, perfect thighs.  My high heels were black patent leather, and I love the way they made my ass look beneath the skirt.  The top held my breasts close and pressed them forward, and the mascara and red lipstick accentuated my face wonderfully.  With my blonde hair, my eyes really popped.  I decided I'd skip the feather duster...for now. Jared's eyes, of course, bulged when he saw me, and he quickly began fidgeting.

"What's the problem, Jared?" I asked, a hint of amusement peeking out from behind a stoic expression.  "Don't you like my outfit?" I asked.

"I, well, um, it looks great," Jared admitted.  That was an understatement!  "But I was supposed to be the sissy," he mumbled.

Towering a few inches over him in my high heels, I slowly slid my hands down my thighs, leaning over to bring my ruby-red lips to eye level with him.  The scent of my perfume wafted over us, and I noticed that he smelled it, a faint smile passing over his lips.

"Do you want to wear this outfit?" I asked him in a low, husky voice.

Jared bit his lip and fidgeted but didn't say anything.  I smiled wickedly.

"I think you do," I said, going to a coat rack nearby.  "Oh, look!" I said, whirling around mischievously with a matching uniform in his size.  "I have a spare!"

Jared's jaw dropped. "Wouldn't you like to put this on?" I asked him, running one of my red-painted fingernails along his neck.  Jared looked at me awkwardly.  I could tell he wanted to, but he didn't want to admit it.  He had certainly been reluctant to admit it to me on the phone.  I took a step back.  If he didn't want to admit it now, fine: I'd draw the confession from him.

"Strip, sissy!" I barked at him.  He jumped in surprise and looked at me nervously.  I held his gaze with my eyes, blue and cold as ice.  As I suspected, he melted in front of me, slowly overcoming his inhibitions and doing as he was told.  I caught the hint of excitement in his movements, the way there seemed to be pent-up energy behind his reluctance.

"Good, sissy," I cooed to him, bending down to give his balls a little stroke.  His cock, already a bit engorged, jumped slightly.

"Now, put this on," I told him gently, handing him the outfit.  He hesitated.

"NOW, sissy!" I ordered, and I slapped him hard on the ass with a riding crop.  He yelped and jumped, but then he obeyed.

I'll admit that the skirt might have been a little short for him.  It might have left his buttocks exposed behind it, and it might have shown an awful lot of his hairy legs.  Of course...that might have been deliberate. "Get on your knees, you little sissy!" I barked at him.  He quickly obeyed; he didn't want to feel my riding crop again.

"Good," I told him.  Standing close to his face, I lifted my skirt, revealing that like him, I wasn't wearing any panties underneath.  He looked up at me uncertainly.

"Sissies are only good for serving," I told him and pulled his head toward my crotch.  My pussy, wet with excitement, glistened in front of him, and the scent of my arousal filled his nostrils.  His cock danced in response, pointing solidly toward the floor.

"You're a pitiful, worthless thing, aren't you?" I asked.  Jared hesitated but nodded.

"I can't hear you, Sissy," I hissed, digging my fingernails into his head.

Jared whimpered, and then murmured, "Yes, Mistress."

"Yes, that's right," I replied, pulling his head in closer.  I let the skirt fall over his head.  "Sissies only live to serve," I reiterated.  "Now lick my pussy and show me respect!"  I pulled his head hard into my crotch, and he struggled at first, caught off-guard.  It didn't take long, though, for him to begin to lick my pussy with little strokes, the feeling of his tongue going over my mound sending little thrills of excitement up my spine.

"Good job, sissy," I complimented him as I pulled his hair back.  He looked disappointed that I'd ended it so quickly, but this wasn't for him.

"I don't care if you were enjoying yourself, Sissy," I told him sternly.  "You have paid your respects, and now your job is to make yourself useful.

"Yes, Mistress," he said, excitement in his voice.

"Bend over, Sissy," I told him.  He bit his lip, but he complied.

"You know that sissies get fucked, don't you?" I said evenly.  His body shuddered, and he nodded.

"Yes, sissies get fucked," I repeated.  I stepped into view and began putting on a dildo harness.

"You're not a man, are you?" I asked him.  He shook his head.

"I can't hear you, Sissy!" I yelled.  He shuddered.

"No, Mistress," he said sullenly.  "I'm not a man."

"Then what are you?"

Jared hesitated.  My crop came down on his ass, adding another red welt to the one there from his last discipline.

"If you want me to drag it out of you, I will!" I barked.

"I'm a sissy," Jared admitted, defeated.

"Yes, you are," I said, squatting down next to his face.  My sex, wet with excitement, must have tempted him from where I was, because I saw him leaning forward, lips extended eagerly.  I tapped his head with the crop.

"Be still," I warned him.  Once he behaved himself, I continued.  "You're a sissy.  You're no longer Jared.  Your name is now Sissy, and that's all you get to be.  And what happens to sissies?"

Sissy swallowed and whispered, "They get fucked."

"What was that?" I asked, running the crop over the welt on his ass as if prepping for another swat.  "I don't think I heard you."

"They get fucked, they get fucked!" Sissy said hurriedly.

"Yes, they do," I replied.  "Which one do you want to fuck you, sissy?" I asked, displaying him an array of dildos.

"The little one," Sissy replied quickly, his eyes wide.

I shook my head and stepped over to him.  Reaching beneath him, I took his nipple between my fingers and pinched it hard.  Sissy cried out in pain as I held my grasp.

"That was the wrong answer, Sissy!" I growled at him, my teeth bared just an inch away from his ear.  "The right answer is, 'whatever you want, Mistress!'  Isn't that right, Sissy?"  I squeezed his nipple harder.

"Yes, Mistress!" Sissy cried.  Tears formed in the corners of his eyes.

"Do you want me to stop pinching your nipple, Sissy?" I asked.

"Yes, Mistress!" Sissy yelled.  I squeezed harder.

"Wrong!  What's the right answer?" I hissed.

"Whatever you want, Mistress!" Sissy groaned.  I released his nipple.  He picked his hand up to cover it.

"Put your hand down!" I ordered and brought my crop down across his back.  A tear fell from his cheek as he put his hand back down.  I leaned over, ran my finger over the tiny puddle on the cold floor and brought my finger to my lips.  Despite his discomfort, Sissy couldn't help but watch as I tasted his salty tear.

"Crying, just like a little sissy," I said, shaking my head.  "Yes, you definitely need to be fucked," I said in a resolved tone.  I went to the dildo rack and chose a medium-sized one.  He'd be able to take it, but it would not be comfortable.

"Pay some respect to this cock," I told him, putting the dildo on and waving it in front of his face.  He moved forward to kiss it, and I wound up my hips and slapped him across the face with it.

"Use your tongue, Sissy!" I told him.  The hit from the dildo wasn't hard enough to leave a mark, but it was certainly enough for his face to sting.  He swallowed nervously and brought his tongue against the rubbery surface.  It was cool and unforgiving, flavorless but erotic as he began to service the cock like a proper sissy should: taking it into his mouth and licking all across the head.

"That's a good sissy," I told him, smiling for the first time since he had arrived.  Running my fingers down under his chin, I pulled his head closer to me to make the dildo go further down his throat.  He gagged, but I held him, making him overcome his reflex.  When I finally released him, he gasped for air, but a dribble of precum below him told me that he was enjoying himself.

"Good, Sissy," I said soothingly, moving over behind him.  I saw him tense.  Donning a glove, I poured cold lube over my hand and let it drool down the crack of his ass, sliming its way around his hole, down his balls, and dripping onto the floor to mix with his precum.  I stroked his hole with my gloved fingers, pushing in slightly.  As I stroked, his hole began to relax, and I was able to push one finger into him, and then two, and then three.  His body writhed against my hand, and he moaned.

"Such a little slut you are," I scoffed behind him.  "Your hole is as loose as a hooker, you little sissy slut!"  That one hit home, and I saw him draw his legs closer together in embarrassment.

I whacked his ass again with the crop, and he jumped.

"How dare you try to close your legs, you little sissy?" I screamed at him.  "This is my hole now!" I said, pushing two fingers into him for emphasis.  His dick throbbed.  "I control what goes in and what comes out!" I added, pulling my fingers out quickly, leaving a gaping void inside of him.  His posture collapsed, but he quickly got back into position.

"Now spread your legs," I told him, tapping the insides of his thighs with my crop.  He complied.

"Good, sissy," I cooed to him, bringing the dildo up to rest on his back.  "Do you feel that?" I asked him.

"Yes, Mistress," he said, his voice quivering with anticipation and nervousness.

"Do you know what that is?" I asked.

"The dildo, Mistress," he replied.

"No, Sissy," I told him.  "That is the cock that is going to take you.  That cock is better than you, and it is going to lower its standards to take a sissy like you, you pathetic little worm."  His cock oozed precum onto the floor.

"Yes, Mistress," Sissy said excitedly.

"And you accept that?" I asked.

"Yes, Mistress," Sissy said breathlessly.

"Do you want this cock inside of you?" I asked, running the dildo through the lube to make it glide over his body.

"Ooh, yes, Mistress," Sissy murmured.  I tapped his back with my crop.

"I mean, whatever you want, Mistress!" Sissy quickly corrected himself.

"Yes, that's right, Sissy," I replied.  I let the dildo circle around his hole a few times, teasing him into thinking he was going to get penetrated, only to move around his ass some.  I could see his body tense each time the dildo came close and relax each time it left, but a growing sense of frustration was making his body get tenser each time.  I let the dildo slip down against his cock.

"It's so much bigger than your little pathetic pinprick," I said dismissively.  "It's way too good for you.  I moved away from him, and he groaned aloud.

"Problem, Sissy?" I asked.  He shook his head but whimpered at the same time.

"What was that?" I prodded.

He huffed and hesitated, but finally, his voice cracking with desire, he whimpered, "No, Mistress.  Whatever you want, Mistress."

Such a good sissy.

I guided the dildo into his ass and pressed in gently.  He wasn't very experienced with ass play, after all, and although I wanted him to be sure of his place, I didn't want to hurt him.  The dildo began to slide in, the ridges on it stretching and widening his ass.  He closed his eyes and groaned as I pressed deeper into him, pushing in and then pulling out.

In my mind, I imagined what this would be like if the cock were real.  I found myself stroking myself from around the harness.  He'd have to get me off for this, I decided.  I continued to thrust into him until I felt the resistance of his buttocks against the harness: the dildo was in to the hilt.

"Good job, Sissy," I praised him, detaching the dildo and leaving it inside of him as I walked around to his head.  "You've found a way to make your sissy pussy useful.  Now make your mouth useful, too."

I unsnapped the harness and let it fall with a clunk against the hard floor.  Stepping over it, I pressed my crotch against his face.  "Get me off, Sissy," I told him, holding his head.

The excitement of being a sissy and the feeling of my dildo in his ass spurred him into action, and he attacked my mound feverishly, smelling and tasting my juices, licking in between my folds to get every drop, and flicking desperately over my clit, hoping that I'd reward him with more of my love serum.

I felt my orgasm rip through my body and pulled his hair hard, burying his face between my folds as I climaxed, giving him a fresh coating of my arousal juices.  Taking a satisfied breath, I released his hair, but he lingered, cleaning me up like a proper sissy would, swallowing every drop.

"Good job, Sissy," I told him when he finished.  "You've earned your feather duster."  He glanced up at me, puzzled, but quickly lowered his eyes.

I reached over behind him and pulled the dildo from him in a fast, fluid motion.  He grunted as it came out, and his posture again collapsed.  I tapped his chest with my crop, and he slowly got back up. Taking a feather duster from among my things, I inserted it handle-first into his ass.  Only the feathers stuck out. "Come and see," I invited him, tapping his buttock with my crop as I led him to a three-way mirror.  Seeing himself this way, dressed in a maid's outfit with the feathers of a feather duster poking out of his ass, the sissy's face turned red, and he looked away. "Look at yourself, Sissy!" I commanded him.  The redness in his face deepened, but he obeyed.  In spite of his embarrassment, his cock was rock hard, partially hidden by the skirt.

"You've earned an orgasm, slave," I told him.  He looked up gratefully as I began to tease my fingers along his aching member.  It took almost no time, and he was off, shooting his cum onto the skirt, just like a good sissy would.